1,2-Dichloroethane → HCID 57650275, compound

HRID 2063468Notes

Reaction equation

HRID 2063468 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([C:17]([OH:19])=O)[CH2:6]1)(=[O:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>C(Cl)Cl>[C:13]([O:12][C:10]([N:8]1[CH2:9][C@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][C@@H:7]1[C:17](=[O:19])[NH:40][CH2:39][C:38]1[CH:41]=[CH:42][C:35]([Cl:34])=[CH:36][CH:37]=1)=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 57650208HCID 57650208, compound

Product 1

HCID 57650275HCID 57650275, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude product (2R,4R)-4-acetoxy-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid from Step A (5.9 g, 21.6 mmol) was dissolved in methylene chloride (22 ml) and treated with EDC (4.5 g, 23.8 mmol) and HOBt (3.2 g, 23.8 mmmol). The mixture was stirred at r.t. for an hour before the addition of 4-chlorobenzylamine (2.9 ml, 23.8 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The mixture was diluted with DCM (25 ml) and washed with NaHCO3 (sat'd) and brine, dried (Na2SO4), filtered, evaporated and the residue purified by silica gel column chromatography (ethyl acetate/hexane gradient, 10-100% EtOAc) to afford the desired product as a white amorphous solid (6.5 g, 76% over two steps).

Workup

  1. washwashed with NaHCO3 (sat'd) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue purified by silica gel column chromatography (ethyl acetate/hexane gradient, 10-100% EtOAc)

Sources & evidence

ORD record
ord-b3d85902181342faa613acb0677e897b
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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